It’s easy to assume that a transgender expert would automatically be the best psychoanalytic choice for someone transitioning their gender identity. But is this true? And what exactly do we mean by trans expert? A relational-constructivist framework places tremendous value on uncertainty and ambiguity, suggesting that too much insistence on sameness and knowing can shut down psychoanalytic exploration. Even trying to be a supportive ally can become paradoxically problematic. Working with my trans patients as a non-expert made generative use of our differences, encouraging the development of mutual recognition and teaching me the value of being “expert enough.”